(2S,3R,4S,5S)-4-Benzyloxy-2-methoxy-6-methylene-tetrahydro-pyran-3,5-diol

Base Information

• Chemical Name: (2S,3R,4S,5S)-4-Benzyloxy-2-methoxy-6-methylene-tetrahydro-pyran-3,5-diol
• CAS No.: 198200-41-8
• Molecular Formula: C₁₄H₁₈O₅
• Molecular Weight: 266.294
• Mol file: 198200-41-8.mol

Synonyms:(2S,3R,4S,5S)-4-Benzyloxy-2-methoxy-6-methylene-tetrahydro-pyran-3,5-diol

Chemical Property of (2S,3R,4S,5S)-4-Benzyloxy-2-methoxy-6-methylene-tetrahydro-pyran-3,5-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4S,5S)-4-Benzyloxy-2-methoxy-6-methylene-tetrahydro-pyran-3,5-diol

There total 3 articles about (2S,3R,4S,5S)-4-Benzyloxy-2-methoxy-6-methylene-tetrahydro-pyran-3,5-diol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 84.0%

Acetic acid (2S,3R,4S,5S)-5-acetoxy-4-benzyloxy-2-methoxy-6-methylene-tetrahydro-pyran-3-yl ester (198200-40-7) → (2S,3R,4S,5S)-4-Benzyloxy-2-methoxy-6-methylene-tetrahydro-pyran-3,5-diol (198200-41-8)

Guidance literature:

With sodium methylate; In methanol; for 1.5h; Ambient temperature;

DOI:10.1016/S0008-6215(97)00149-3

Reference yield:

methyl 3-O-benzyl-6-deoxy-6-iodo-α-D-glucopyranoside (198200-37-2) → (2S,3R,4S,5S)-4-Benzyloxy-2-methoxy-6-methylene-tetrahydro-pyran-3,5-diol (198200-41-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / pyridine / 2 h / Ambient temperature

2: 74 percent / DBU / dimethylformamide / 2.5 h / 75 °C

3: 84 percent / NaOMe / methanol / 1.5 h / Ambient temperature

With pyridine; sodium methylate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(97)00149-3

Reference yield:

methyl 2,4-di-O-acetyl-3-O-benzyl-6-deoxy-6-iodo-α-D-glucopyranoside (198200-38-3) → (2S,3R,4S,5S)-4-Benzyloxy-2-methoxy-6-methylene-tetrahydro-pyran-3,5-diol (198200-41-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 74 percent / DBU / dimethylformamide / 2.5 h / 75 °C

2: 84 percent / NaOMe / methanol / 1.5 h / Ambient temperature

With sodium methylate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(97)00149-3

upstream raw materials:

Acetic acid (2S,3R,4S,5S)-5-acetoxy-4-benzyloxy-2-methoxy-6-methylene-tetrahydro-pyran-3-yl ester

methyl 3-O-benzyl-6-deoxy-6-iodo-α-D-glucopyranoside

methyl 2,4-di-O-acetyl-3-O-benzyl-6-deoxy-6-iodo-α-D-glucopyranoside

Downstream raw materials:

methyl 3-O-benzyl-6-deoxy-6-iodo-α-D-glucopyranoside

(2R,3S,4R,5R,6S)-4-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-6-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester

(2R,3S,4S,5R,6S)-5-Benzoyloxy-4-benzyloxy-3-hydroxy-6-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester

2,2-Dimethyl-propionic acid (2S,3R,4R,5S)-4-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-6-methylene-tetrahydro-pyran-3-yl ester